Phenyl-substituted 5,6-dihydropyrone derivatives for use as pesticides and herbicides

ABSTRACT

The present invention relates to novel phenyl-substituted 5,6-dihydro-pyrone derivatives of the formula (I) 
                 
 
in which
 
W, X, Y, Z, G, A, B, Q 1  and Q 2  are each as defined in the description,
 
to a plurality of processes for their preparation and to their use as pesticides and herbicides.

The present invention relates to novel phenyl-substituted5,6-dihydro-pyrone derivatives, to a plurality of processes for theirpreparation and to their use as pesticides and herbicides.

It is known that certain 5,6-dihydropyrone derivatives have, as proteaseinhibitors, antiviral properties: WO 95/14012. Furthermore,4-phenyl-6-(2-phenethyl)-5,6-dihydropyrone is known from the synthesisof kavalactone derivatives: Kappe et al.; Arch. Pharm. 309, 558-64,(1976). Moreover, 5,6-dihydropyrone derivatives are known asintermediates: White, J. D., Brenner, J. B., Deinsdale, M. J., J. Amer.Chem. Soc. 93, 281-2 (1971). Applications in crop protection havehitherto not been described.

This invention now provides novel compounds of the formula (I)

in which

-   W represents hydrogen, alkyl, alkenyl, alkinyl, halogen,    halogenoalkyl or alkoxy,-   X represents halogen, alkyl, alkoxy, alkenyl, alkinyl,    halogenoalkyl, halogenoalkoxy, cyano or in each case optionally    substituted phenyl, phenoxy, phenylthio, phenylalkoxy or    phenylalkylthio,-   Y represents hydrogen, alkyl, halogen, halogenoalkyl, alkoxy,    alkenyl, alkinyl or optionally substituted aryl or hetaryl,-   Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,    halogenoalkoxy or cyano,-   A represents a bond, hydrogen, in each case optionally    halogen-substituted alkyl, alkenyl, alkoxyalkyl, optionally    substituted cycloalkyl or cycloalkylalkyl in which optionally at    least one ring atom is replaced by a hetero atom, or in each case    optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-,    halogenoalkoxy-, cyano- or nitro-substituted aryl, arylalkyl,    hetaryl or hetarylalkyl,-   B represents hydrogen or alkyl, or-   A and B together with the carbon atom to which they are attached    represent a saturated or unsaturated unsubstituted or substituted    cycle which optionally contains at least one hetero atom, or-   B and Q¹ together represent alkanediyl which is optionally    substituted by in each case optionally substituted alkyl or alkoxy    and in which two not directly adjacent carbon atoms optionally form    a further optionally substituted cycle or-   Q¹ represents hydrogen, hydroxyl, alkyl, alkoxy, alkoxyalkyl,    alkylacyloxy, optionally substituted cycloalkyl (in which optionally    one methylene group is replaced by oxygen or sulphur) or optionally    substituted phenyl,-   Q² represents hydrogen or alkyl, or-   Q¹ and Q² together with the carbon atom to which they are attached    represent an unsubstituted or substituted cycle which optionally    contains a hetero atom,-   G represents hydrogen (a) or represents one of the groups    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur,    -   M represents oxygen or sulphur,    -   R¹ represents in each case optionally halogen-substituted alkyl,        alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or        optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl in        which one or more methylene groups may be replaced by hetero        atoms, in each case optionally substituted phenyl, phenylalkyl,        hetaryl, phenoxyalkyl or hetaryloxyalkyl,    -   R² represents in each case optionally halogen-substituted alkyl,        alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case        optionally substituted cycloalkyl, phenyl or benzyl,    -   R³, R⁴ and R⁵ independently of one another each represent in        each case optionally halogen-substituted alkyl, alkoxy,        alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio        and represent in each case optionally substituted phenyl,        benzyl, phenoxy or phenylthio, and    -   R⁶ and R⁷ independently of one another each represent hydrogen,        in each case optionally halogen-substituted alkyl, cycloalkyl,        alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted        phenyl, represent optionally substituted benzyl, or together        with the N atom to which they are attached represent a ring        which is optionally interrupted by oxygen or sulphur.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if required, can beseparated in a customary manner. The invention provides both the pureisomers and the isomer mixtures, their preparation and use, andcompositions comprising them. Hereinbelow, for the sake of simplicity,only compounds of the formula (I) are referred to, although this maymean both the pure compounds and, if appropriate, also mixturescontaining different percentages of isomeric compounds.

Depending on the position of the substituent G, the compounds of theformula (I) can be present in the two isomeric forms of the formulae(I-A) and (I-B)

which is meant to be indicated by the broken line in formula (I).

The compounds of the formulae (I-A) and (I-B) can be present either asmixtures or in the form of their pure isomers. Mixtures of the compoundsof the formulae (I-A) and (I-B) can, if required, be separated in amanner known per se by physical methods, for example by chromatographicmethods.

For reasons of clarity, only one of the possible isomers is shownhereinbelow. This does not exclude that the compounds may, ifappropriate, be present in the form of the isomer mixtures or therespective other isomeric form.

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) ofgroup G, the following principal structures (I-a) to (I-g) result:

in whichA, B, E, L, M, Q¹, Q², W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

Furthermore, it has been found that the novel compounds of the formula(I) can be obtained by one of the processes described below:

-   (A) substituted 5,6-dihydropyrones of the formula (I-a)    -   in which    -   A, B, Q¹, Q², W, X, Y and Z are each as defined above, can be        obtained when    -   O-acylhydroxycarboxylic esters of the formula (II)    -   in which    -   A, B, Q¹, Q², W, X, Y and Z are each as defined above,    -   and    -   R⁸ represents alkyl (preferably C₁-C₆-alkyl),    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base.

Furthermore, it has been found

-   (B) that compounds of the formulae (I-a) to (I-g) shown above in    which A, B, G, Q¹, Q², W, X, Y and Z are each as defined above are    obtained when compounds of the formulae (I-a′) to (I-g′),    -   in which    -   A, B, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, E, L, M, Q¹, Q², W′, X′, Y′        and Z′ each have the meanings of W, X, Y and Z given above and        where at least one of the radicals    -   W′, X′, Y′ represents chlorine, bromine or iodine, preferably        bromine,    -   and Z′ does not represent bromine or iodine,    -   α) are initially reacted with silylacetylene of the formula        (III)        -   in which        -   R⁹ represents hydrogen and        -   R¹⁰ represents C₁-C₄-alkyl or phenyl, in particular methyl            or tert-butyl,        -   in the presence of a solvent, a base and a catalyst,            suitable catalysts being, in particular, palladium            complexes, and the silyl group is subsequently removed,    -   or    -   β) are reacted with vinylstannanes of the formula (IV)        -   in which        -   R⁹ represents hydrogen, methyl or ethyl and        -   R¹⁰ represents C₁-C₄-alkyl, in particular butyl,        -   in the presence of a solvent, if appropriate in the presence            of a base and in the presence of a catalyst, suitable            catalysts being, in particular, palladium complexes,    -   or    -   γ) in the specific case where Y′ represents chlorine, bromine or        iodine, preferably bromine, and W′, X′ and Z′ do not represent        bromine or iodine, are reacted with boronic acids of the formula        (V)        -   in which        -   Y represents optionally substituted phenyl or hetaryl,        -   in the presence of a solvent, a base and a catalyst,            suitable catalysts being, in particular, palladium            complexes.

Moreover, it has been found

-   (C) that the compounds of the formula (I-b) shown above in which A,    B, Q¹, Q², R¹, W, X, Y and Z are each as defined above are obtained    when compounds of the formula (I-a) shown above in which A, B, Q¹,    Q², W, X, Y and Z are each as defined above are in each case reacted    -   (α) with acyl halides of the formula (VI)        -   in which        -   R¹ is as defined above and        -   Hal represents halogen (in particular chlorine or bromine)        -   or    -   (β) with carboxylic anhydrides of the formula (VII)        R¹—CO—O—CO—R¹  (VII)        -   in which        -   R¹ is as defined above,        -   if appropriate in the presence of a diluent and if            appropriate in the presence of an acid binder;-   (D) that the compounds of the formula (I-c) shown above in which A,    B, Q¹, Q², R², M, W, X, Y and Z are each as defined above and L    represents oxygen are obtained when the compounds of the formula    (I-a) shown above in which A, B, Q¹, Q², W, X, Y and Z are each as    defined above are in each case reacted    -   with chloroformic esters or chloroformic thioesters of the        formula (VIII)        R²-M-CO—Cl  (VIII)    -   in which    -   R² and M are each as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;-   (E) that compounds of the formula (I-c) shown above in which A, B,    Q¹, Q², R², M, W, X, Y and Z are each as defined above and L    represents sulphur are obtained when compounds of the formula (I-a)    shown above in which A, B, Q¹, Q², W, X, Y and Z are each as defined    above are in each case reacted    -   with chloromonothioformic esters or chlorodithioformic esters of        the formula (IX)    -   in which    -   M and R² are each as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,    -   and-   (F) that compounds of the formula (I-d) shown above in which A, B,    Q¹, Q², R³, W, X, Y and Z are each as defined above are obtained    when compounds of the formula (I-a) shown above in which A, B, Q¹,    Q², W, X, Y and Z are each as defined above are in each case reacted    -   with sulphonyl chlorides of the formula (X)        R³—SO₂—Cl  (X)    -   in which    -   R³ is as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,-   (G) that compounds of the formula (I-e) shown above in which A, B,    L, Q¹, Q², R⁴, R⁵, W, X, Y and Z are each as defined above are    obtained when compounds of the formula (I-a) shown above in which A,    B, Q¹, Q², W, X, Y and Z are each as defined above are in each case    reacted    -   with phosphorus compounds of the formula (XI)    -   in which    -   L, R⁴ and R⁵ are each as defined above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,-   (H) that compounds of the formula (I-f) shown above in which A, B,    E, Q¹, Q², W, X, Y and Z are each as defined above are obtained when    compounds of the formula (I-a) shown above in which A, B, Q¹, Q², W,    X, Y and Z are each as defined above are in each case reacted    -   with metal compounds or amines of the formula (XII) or (XIII)

Me(OR¹¹)_(t)  (XII)

-   -   in which    -   Me represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹¹, R¹², R¹³ independently of one another each represent        hydrogen or alkyl (preferably C₁-C₈-alkyl),    -   if appropriate in the presence of a diluent,

-   (I) that compounds of the formula (I-g) show above in which A, B, L,    Q¹, Q², R⁶, R⁷, W, X, Y and Z are each as defined above are obtained    when compounds of the formula (I-a) shown above in which A, B, Q¹,    Q², W, X, Y and Z are each as defined above are in each case    -   (α) reacted with isocyanates or isothiocyanates of the formula        (XIV)        R⁶—N═C═L  (XIV)        -   in which        -   R⁶ and L are each as defined above,        -   if appropriate in the presence of a diluent and if            appropriate in the presence of a catalyst or    -   (β) are reacted with carbamoyl chlorides or thiocarbamoyl        chlorides of the formula (XV)        -   in which        -   L, R⁶ and R⁷ are each as defined above,        -   if appropriate in the presence of a diluent and if            appropriate in the presence of an acid binder.

Furthermore, it has been found that 5,6-dihydropyrone derivatives of theformula (I) can be prepared by reacting

-   J) silyl enol ethers of the formula    -   in which    -   A and B are each as defined above and    -   Alk represents alkyl having 1 to 4 carbon atoms,    -   in each case with ketene derivatives of the formula    -   in which    -   W, X, Y and Z are each as defined above and    -   Hal represents chlorine or bromine,        if appropriate in the presence of a diluent or a diluent mixture        and if appropriate in the presence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticides,acaricides and also as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   W preferably represents hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl,    ethinyl, fluorine, chlorine, bromine, C₁-C₄-halogenoalkyl or    C₁-C₆-alkoxy,-   X preferably represents fluorine, chlorine, bromine, C₁-C₆-alkyl,    C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₂-C₄-alkenyl, ethinyl,    C₁-C₄-halogenoalkoxy, cyano or in each case optionally halogen-,    C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,    C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl or    benzyloxy,-   Y preferably represents hydrogen, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl,    fluorine, chlorine, bromine, C₁-C₆-alkoxy, C₂-C₄-alkenyl, ethinyl or    represents one of the radicals-   V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₄-halogenoalkyl,    C₁-C₄-halogenoalkoxy, nitro, cyano or represents phenyl, phenoxy,    phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl or    phenyl-C₁-C₄-alkylthio, each of which is optionally mono- or    polysubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,-   V² preferably represents hydrogen, fluorine, chlorine, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy,-   V³ preferably represents hydrogen, fluorine, chlorine, methyl or    methoxy,-   Z preferably represents hydrogen, fluorine, chlorine, bromine,    C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkoxy    or cyano,    -   with the first proviso, that W, X and Z do not represent        bromine, C₂-C₄-alkenyl and ethinyl if Y represents V¹-, V²- and        V³-substituted phenyl or hetaryl and that secondly only at most        two of the radicals W, X and Y represent C₂-C₄-alkenyl or        ethinyl, with the proviso that none of the other radicals W, X,        Y and Z may represent bromine,    -   A preferably represents a bond, hydrogen or in each case        optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,        C₁-C₆-alkoxy-C₁-C₄-alkyl, in each case optionally halogen-,        C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or        C₃-C₆-cycloalkyl-C₁-C₄-alkyl in which optionally one or two not        directly adjacent ring members are replaced by oxygen and/or        sulphur or represents in each case optionally halogen-,        C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,        C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl,        benzyl, hetaryl having 5 or 6 ring atoms (for example furanyl,        pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl, thiazolyl        or thienyl) or hetaryl-C₁-C₄-alkyl having 5 or 6 ring atoms (for        example pyridyl, pyrimidyl or thiazolyl),-   B preferably represents hydrogen or C₁-C₆-alkyl, or-   A, B and the carbon atom to which they are attached preferably    represent saturated C₃-C₁₀-cycloalkyl or unsaturated    C₅-C₁₀-cycloalkyl in which optionally one ring member is replaced by    oxygen or sulphur and which are optionally mono- or disubstituted by    C₁-C₆-alkyl, C₃-C₈-cycloalkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, halogen or phenyl, with the proviso that Q¹ and Q²    do not form a further cycle, or-   B and Q¹ together preferably represent C₃-C₆-alkanediyl which is    optionally mono- or disubstituted by identical or different    C₁-C₄-alkyl and in which two not directly adjacent carbon atoms    optionally form a further 3- to 6-membered cycle, or-   Q¹ preferably represents hydrogen, hydroxyl, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₂-alkyl, C₁-C₆-alkylacyloxy,    optionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-    or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one    methylene group is replaced by oxygen or sulphur or optionally    halogen, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,    C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl,-   Q² preferably represents hydrogen or C₁-C₄-alkyl, or-   Q¹ and Q² together with the carbon atom to which they are attached    preferably represent optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy- or    C₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally    one ring member is replaced by oxygen or sulphur, with the proviso    that A and B do not form a further cycle,-   G represents hydrogen (a) or represents one of the groups-    E (f) or-    in particular (a), (b) or (c),-   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur.-   R¹ preferably represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl,    C₁-C₈-alkylthio-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or    optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted    C₃-C₈-cycloalkyl in which optionally one or more (preferably one or    two) not directly adjacent ring members are replaced by oxygen    and/or sulphur, or    -   represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,        C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl, or    -   represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,        C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or        C₁-C₆-halogenoalkoxy-substituted phenyl-C₁-C₆-alkyl, or    -   represents optionally halogen-, C₁-C₆-alkyl- or        trifluoromethyl-substituted 5- or 6-membered hetaryl (for        example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or        thienyl), or    -   represents optionally halogen- or C₁-C₆-alkyl-substituted        phenoxy-C₁-C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁-C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁-C₆-alkyl        (for example pyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl or        thiazolyloxy-C₁-C₆-alkyl),-   R² preferably represents in each case optionally halogen-substituted    C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₂-C₈-alkyl,    poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, or    -   represents optionally halogen-, C₁-C₆-alkyl- or        C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or        C₁-C₆-halogenoalkoxy-substituted phenyl or benzyl,-   R³ preferably represents optionally halogen-substituted C₁-C₈-alkyl    or represents in each case optionally halogen-, C₁-C₆-alkyl-,    C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano-    or nitro-substituted phenyl or benzyl,-   R⁴ and R⁵ independently of one another each preferably represent in    each case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,    C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,    C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each case    optionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,    C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,    C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, benzyl,    phenoxy or phenylthio,-   R⁶ and R⁷ independently of one another each preferably represent    hydrogen, represent in each case optionally halogen-substituted    C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,    C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,    C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted    phenyl, optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or    C₁-C₈-alkoxy-substituted benzyl or together represent an optionally    C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally    one carbon atom is replaced by oxygen or sulphur.

In the radical definitions mentioned as being preferred, halogen, alsoas substituent such as, for example, in halogenoalkyl, representsfluorine, chlorine, bromine and iodine, in particular fluorine andchlorine.

-   W particularly preferably represents hydrogen, C₁-C₄-alkyl, chlorine    or bromine,-   X particularly preferably represents chlorine, bromine, C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₂-C₃-alkenyl, ethinyl, C₁-C₂-halogenoalkyl,    C₁-C₂-halogenoalkoxy or cyano,-   Y particularly preferably represents hydrogen, C₁-C₄-alkyl,    C₁-C₂-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₄-alkoxy,    C₂-C₃-alkenyl, ethinyl, 2-thienyl, 3-thienyl or represents the    radical-   V¹ particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,    C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro, cyano or phenyl,-   V² particularly preferably represents hydrogen, fluorine, chlorine,    C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₂-halogenoalkyl,-   Z particularly preferably represents hydrogen, fluorine, chlorine,    bromine, C₁-C₄-alkyl, C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy or    C₁-C₂-halogenoalkoxy,    -   with the first proviso that W, X and Z do not represent bromine,        C₂-C₃-alkenyl and ethinyl if Y represents V¹- and V²-substituted        phenyl, 2-thienyl or 3-thienyl and that secondly only one of the        radicals X and Y represents C₂-C₃-alkenyl and ethinyl, with the        proviso that in this case none of the other radicals W, X, Y and        Z may represent bromine,-   A particularly preferably represents a bond, hydrogen, in each case    optionally fluorine-substituted C₁-C₈-alkyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, in each case optionally fluorine-,    chlorine-, methyl-, ethyl- or methoxy-substituted C₅-C₆-cycloalkyl    or C₃-C₆-cycloalkyl-C₁-C₂-alkyl in which optionally one ring member    is replaced by oxygen or sulphur or in each case optionally    fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-,    C₁-C₄-alkoxy- or C₁-C₂-halogenoalkoxy-substituted phenyl or benzyl,-   B particularly preferably represents hydrogen or C₁-C₄-alkyl, or-   A, B and the carbon atom to which they are attached particularly    preferably represent saturated C₅-C₇-cycloalkyl in which optionally    one ring member is replaced by oxygen and which is optionally    monosubstituted by C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy,    with the proviso that Q¹ and Q² do not form a further cycle, or-   B and Q¹ together particularly preferably represent C₃-C₄-alkanediyl    which is optionally monosubstituted by C₁-C₂-alkyl and in which two    not directly adjacent carbon atoms optionally form a further five-    or six-membered cycle, or-   Q¹ particularly preferably represents hydrogen, hydroxyl,    C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,    C₁-C₄-alkylacyloxy or optionally methyl- or methoxy-substituted    C₃-C₆-cycloalkyl in which optionally one methylene group is replaced    by oxygen,-   Q² particularly preferably represents hydrogen, methyl or ethyl, or-   Q¹ and Q² particularly preferably together with the carbon to which    they are attached represent optionally C₁-C₄-alkyl-,    trifluoromethyl- or C₁-C₄-alkoxy-substituted saturated    C₅-C₆-cycloalkyl in which optionally one ring member is replaced by    oxygen, with the proviso that A and B do not form a further cycle,-   G particularly preferably represents hydrogen (a) or represents one    of the groups-    E (f) or-    in particular (a), (b) or (c),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,-   R¹ particularly preferably represents in each case optionally    fluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,    C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl, or optionally    fluorine-, chlorine-, C₁-C₂-alkyl-, or C₁-C₂-alkoxy-substituted    C₃-C₇-cycloalkyl in which optionally one or two not directly    adjacent ring members are replaced by oxygen and/or sulphur, or    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl,        C₁-C₄-alkoxy, trifluoromethyl or trifluoromethoxy, or    -   represents pyridyl or thienyl, each of which is optionally        monosubstituted by fluorine, chlorine, bromine, methyl, ethyl or        trifluoromethyl,-   R² particularly preferably represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl    or C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine, or    -   represents C₃-C₇-cycloalkyl which is optionally monosubstituted        by methyl, ethyl or methoxy, or    -   represents phenyl or benzyl, each of which is optionally mono-        or disubstituted by fluorine, chlorine bromine, cyano, nitro,        C₁-C₄-alkyl, C₁-C₃-alkoxy, trifluoromethyl or trifluoromethoxy,-   R³ particularly preferably represents C₁-C₆-alkyl which is    optionally mono- to pentasubstituted by fluorine or represents    phenyl which is optionally mono- or disubstituted by fluorine,    chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl,    trifluoromethoxy, cyano or nitro,-   R⁴ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, or    represents phenyl, benzyl, phenoxy or phenylthio, each of which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    nitro, cyano, C₁-C₃-alkoxy, trifluoromethoxy, C₁-C₃-alkyl or    trifluoromethyl,-   R⁵ particularly preferably represents C₁-C₄-alkyl, C₁-C₄-alkoxy or    C₁-C₄-alkylthio,-   R⁶ particularly preferably represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, or represents    phenyl which is optionally mono- or disubstituted by fluorine,    chlorine, bromine, trifluoromethyl, C₁-C₄-alkyl or C₁-C₄-alkoxy, or    represents benzyl which is optionally mono- or disubstituted by    fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or    methoxy,-   R⁷ particularly preferably represents hydrogen, C₁-C₆-alkyl or    C₃-C₆-alkenyl, or-   R⁶ and R⁷ together particularly preferably represent a    C₄-C₅-alkylene radical which is optionally mono- or disubstituted by    methyl or ethyl and in which optionally one methylene group is    replaced by oxygen or sulphur.

In the radical definitions mentioned as being particularly preferred,halogen, also as substituent, such as, for example, in halogenoalkyl,represents fluorine, chlorine, bromine and iodine, in particularfluorine or chlorine, particularly preferably fluorine.

-   W very particularly preferably represents hydrogen, chlorine,    bromine, methyl or ethyl,-   X very particularly preferably represents chlorine, bromine, methyl,    ethyl, n-propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy,    trifluoromethoxy or cyano (especially chlorine, bromine, methyl,    ethyl, n-propyl or trifluoromethyl),-   Y very particularly preferably represents hydrogen, methyl, ethyl,    propyl, iso-propyl, trifluoromethyl, fluorine, chlorine, bromine,    methoxy or represents the radical-   V¹ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, iso-propyl, tert-butyl, methoxy,    trifluoromethyl or trifluoromethoxy cyano or phenyl,-   V² very particularly preferably represents hydrogen, fluorine,    chlorine, methyl or trifluoromethyl,-   Z very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, methoxy or trifluoromethyl (especially    hydrogen, fluorine, chlorine, bromine or methyl), with the proviso    that W, X and Z do not represent bromine if Y represents V¹- and    V²-substituted phenyl,-   A very particularly preferably represents a bond, hydrogen, methyl,    ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl,-   B very particularly preferably represents hydrogen, methyl or ethyl,    or-   A, B and the carbon atoms to which they are attached very    particularly preferably represent saturated C₅-C₆-cycloalkyl in    which optionally one ring member is replaced by oxygen and which is    optionally monosubstituted by methyl, ethyl, methoxy or ethoxy, with    the proviso that Q¹ and Q² do not form a further cycle or-   B and Q¹ together very particularly preferably represent    C₃-C₄-alkanediyl which is optionally monosubstituted by methyl and    in which two not directly adjacent carbon atoms optionally form a    further three- to six-membered cycle, or-   Q¹ very particularly preferably represents hydrogen, hydroxyl,    methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, propoxy,    acetyloxy or propionyloxy,-   Q² very particularly preferably represents hydrogen, methyl or    ethyl, or-   Q¹ and Q² together with the carbon to which they are attached very    particularly preferably represent saturated C₆-cycloalkyl which is    optionally substituted by methyl, ethyl, methoxy, ethoxy, propoxy or    butoxy and in which optionally one ring member is replaced by    oxygen, with the proviso that A and B do not form a further cycle,-   G very particular preferably represents hydrogen (a) or represents    one of the groups-    E (f) or-    in particular (a), (b) or (c),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen (particularly preferably in the case of (c))        or sulphur and    -   M represents oxygen or sulphur,-   R¹ very particularly preferably represents in each case optionally    fluorine- or chlorine-substituted C₁-C₈-alkyl, C₂-C₈-alkenyl,    C₁-C₂-alkoxy-C₁-alkyl, C₁-alkylthio-C₁-alkyl, cyclopropyl,    cyclopentyl or cyclohexyl or    -   represents phenyl which is optionally monosubstituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl,        iso-propyl, tert-butyl, methoxy, trifluoromethyl or        trifluoromethoxy, or    -   represents thienyl or pyridyl, each of which is optionally        monosubstituted by chlorine, bromine or methyl,-   R² very particularly preferably represents C₁-C₈-alkyl,    C₂-C₈-alkenyl or C₁-C₄-alkoxy-C₂-alkyl, or cyclohexyl    -   or represents phenyl or benzyl, each of which is optionally        monosubstituted by fluorine, chlorine, bromine, cyano, nitro,        methyl, tert-butyl, methoxy, trifluoromethyl or        trifluoromethoxy,-   R³ very particularly preferably represents methyl, ethyl, n-propyl,    or phenyl which is optionally monosubstituted by fluorine, chlorine,    bromine, methyl, tert-butyl, methoxy, trifluoromethyl,    trifluoromethoxy, cyano or nitro,-   R⁴ very particularly preferably represents C₁-C₄-alkyl,    C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,    C₁-C₄-alkylthio or represents phenyl, phenoxy or phenylthio, each of    which is optionally monosubstituted by fluorine, chlorine, bromine,    nitro, cyano, C₁-C₂-alkoxy, trifluoromethoxy or C₁-C₃-alkyl,-   R⁵ very particularly preferably represents methyl, ethyl, methoxy,    ethoxy, methylthio or ethylthio,-   R⁶ very particularly preferably represents C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl,-   R⁷ very particularly preferably represents hydrogen, C₁-C₄-alkyl or    C₃-C₄-alkenyl, or-   R⁶ and R⁷ together very particularly preferably represent a    C₆-alkylene radical in which optionally one methylene group is    replaced by oxygen or sulphur,-   W most preferably represents hydrogen, methyl, ethyl, chlorine or    bromine,-   X most preferably represents methyl, ethyl, n-propyl,    trifluoromethyl or chlorine,-   Y most preferably represents methyl, trifluoromethyl, chlorine,    bromine, represents phenyl which is optionally mono- or    disubstituted by chlorine and/or methyl,-   Z most preferably represents hydrogen or methyl, with the proviso    that W does not represent bromine if Y represents substituted    phenyl,-   A most preferably represents methyl, ethyl or a bond,-   B most preferably represents methyl or ethyl or-   A and B and the carbon atom to which they are attached most    preferably represent cyclopropyl or cyclohexyl, or-   B and Q¹ together most preferably represent C₄-alkanediyl which is    monosubstituted by methyl,-   Q¹ most preferably represents hydrogen, methyl, methoxy, ethoxy,    propoxy, hydroxyl or acetyloxy,-   Q² most preferably represents hydrogen or methyl,-   G most preferably represents hydrogen (a) or represents one of the    groups-   where-   R¹ most preferably represents C₁-C₄-alkyl or represents phenyl or    pyridyl, each of which is optionally monosubstituted by chlorine,-   R² most preferably represents C₁-C₄-alkyl.

The general or preferred radical definitions or explanations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Most preference according to the invention is given to the compounds ofthe formula (I) which contain a combination of the meanings listed aboveas being most preferred.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenylcan in each case be straight-chain or branched as far as this ispossible, including in combination with hetero atoms, such as, forexample, in alkoxy.

Unless indicated otherwise, optionally substituted radicals can be mono-or polysubstituted, and in the case of polysubstitution, thesubstituents can be identical or different.

Using, according to process (A), ethyl O-[(2,4-dichloro)-phenylacetyl]1-hydroxy-methyl-cyclohexane-carboxylate as starting material, thecourse of the process according to the invention can be represented bythe following reaction scheme:

Using, according to process (Bγ),3-[(2-chloro-4-bromo-6-methyl)-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyroneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

Using, according to process (Cα),3-[(2,4-dichloro)-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyrone andpivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, according to process (Cβ),3-[(4-bromo-2-chloro-6-ethyl)-phenyl]-6,6-dimethyl-5,6-dihydropyrone andacetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

Using, according to process (D),3-[(2-chloro-6-ethyl-4-phenyl)-phenyl]-5,5-dimethyl-5,6-dihydropyroneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

Using, according to process (E),3-[2,4,6-trichloro-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyrone andmethyl chloromonothioformate as starting materials, the course of thereaction can be represented as follows:

Using, according to process (F),3-(4-chloro-2-methyl-phenyl)-5,5-dimethyl-6-methoxy-5,6-dihydropyroneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following reaction scheme:

Using, according to process (G),2-(2-methyl-5-bromo-phenyl)-5,5,6,6-tetramethyl-5,6-dihydropyrone and2,2,2-trifluoroethyl methanethio-phosphonate as starting materials, thecourse of the reaction can be represented by the following reactionscheme:

Using, according to process (H),3-(2,4-dichloro-phenyl)-5,5-pentamethylene-6-methoxy-5,6-dihydropyroneand NaOH as components, the course of the process according to theinvention can be represented by the following reaction scheme:

Using, according to process (Iα),3-(2,4-dichloro-phenyl)-5,5,6,6-tetramethyl-5,6-dihydropyrone and ethylisocyanate as starting materials, the course of the reaction can berepresented by the following reaction scheme:

Using, according to process (I•),3-(2-chloro-4-bromo-phenyl)-5,5-dimethyl-6-methoxy-5,6-dihydropyrone anddimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

Using chlorocarbonyl 2-mesitylene ketene andtrimethyl-silyloxymethylidene-cyclohexane as starting materials, thecourse of the process (J) according to the invention can be representedby the following formula scheme:

The compounds of the formula (II)

-   in which-   A, B, Q¹, Q², W X, Y, Z and R⁸ are each as defined above,-   required as starting materials in the process (A) according to the    invention are novel.

The acylhydroxycarboxylic esters of the formula (II) are obtained, forexample, when hydroxycarboxylic esters of the formula (XVIII)

-   in which-   A, B, Q¹, Q² and R⁸ are each as defined above,-   are acylated with substituted phenylacetyl halides of the formula    (XIX)-   in which-   W, X, Y and Z are each as defined above and-   Hal represents chlorine or bromine,    (see Preparation Examples for compounds of the formula (II)).

Some of the compounds of the formula (XVIII) are known, or they can beprepared by processes known in principle, for example by Reformatskijsynthesis (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin1990, 18^(th) edition, p. 501 ff.).

Some of the compounds of the formula (XIX) are known and commerciallyavailable. They can be prepared by processes known in principle (see,for example, H. Henecka, Houben-Weyl, Methoden der Organischen Chemie[Methods of Organic Chemistry], Vol. 8, pp. 467-469 (1952), WO 97/02243,WO 99/43649).

The compounds of the formula (XIX) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XX)

-   in which-   W, X, Y and Z are each as defined above,-   with halogenating agents (for example thionyl chloride, thionyl    bromide, oxalyl chloride, phosgene, phosphorus trichloride,    phosphorus tribromide or phosphorus pentachloride), if appropriate    in the presence of a diluent (for example optionally chlorinated    aliphatic or aromatic hydrocarbons, such as toluene or methylene    chloride), at temperatures of from −20° C. to 150° C., preferably    from −10° C. to 100° C.

Some of the compounds of the formula (XX) are commercially available,some are known, or they can be prepared by processes known in principle(for example WO 97/02243, WO 99/43649).

Some of the silylacetylenes of the formula (III) required for carryingout the process B(α) are commercially available, or they can be preparedby generally known processes. Some of the vinylstannanes of the formula(IV) required for carrying out the process B(β) are likewisecommercially available, or they can be prepared by known processes.

Some of the boronic acids of the formula (V)

-   in which-   Y represents optionally substituted phenyl or hetaryl,-   required for carrying out the process B(γ) are commercially    available, or they can be prepared in a simple manner by generally    known processes.

The formula (XVI) provides a general definition of the silyl enol ethersrequired as starting materials for carrying out the process (J)according to the invention. In this formula, A and B each preferablyhave those meanings which have already been mentioned in connection withthe description of the 5,6-dihydro-pyrones of the formula (I) accordingto the invention as being preferred for these radicals. Alk preferablyrepresents methyl or ethyl, particularly preferably methyl.

The silyl enol ethers of the formula (XVI) are known or can be preparedby known methods.

The formula (XIV) provides a general definition of the ketenederivatives required as reaction components for carrying out the processaccording to the invention. In this formula, W, X, Y and Z eachpreferably have those meanings which have already been mentioned inconnection with the description of the 5,6-dihydro-pyrones of theformula (I) according to the invention as being preferred for theseradicals. Hal also preferably represents chlorine or bromine.

Ketene derivatives of the formula (XVII) are known or can be prepared byknown processes (cf. Org. Prep. Proced. Int. 7, 155-158 (1975) and DE-A1 945 703). Thus, ketene derivatives of the formula (XVII) are obtainedby reacting

-   substituted phenylmalonic acids of the formula (XXI)-   in which-   W, X, Y and Z are each as defined above,-   with acid halides, such as, for example, thionyl chloride,    phosphorus(V) chloride, phosphorus(III) chloride, oxalyl chloride,    phosgene or thionyl bromide, if appropriate in the presence of    catalysts, such as, for example, diethylformamide,    methyl-stearyl-formamide or triphenylphosphine and if appropriate in    the presence of bases such as, for example, pyridine or    triethylamine, at a temperature between −20° C. and +200° C.,    preferably between 0° C. and 150° C.

The substituted phenylmalonic acids of the formula (XXI) are known orcan be prepared by known methods (cf., for example, Organikum, VEBDeutscher Verlag der Wissenschaften, Berlin 1977, p. 517 ff.). Thus,substituted phenylmalonic acids of the formula (XXI) are obtained byreacting substituted phenylmalonic esters of the formula

-   in which-   W, X, Y and Z are each as defined above and-   R⁹ represents alkyl having 1 to 4 carbon atoms,-   with alkali metal hydroxides, such as sodium hydroxide or potassium    hydroxide, in the presence of a diluent, such as water, at    temperatures between 0° C. and 30° C.

In the formula (XXII), W, X, Y and Z each preferably have those meaningswhich have already been mentioned in connection with the description ofthe 5,6-dihydro-pyrones of the formula (I) according to the invention asbeing preferred for these radicals. R⁹ preferably represents methyl orethyl.

The substituted phenylmalonic esters of the formula (XXII) are known orcan be prepared by known methods (cf. Tetrahedron Letters 27, 2763(1986) and Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin1977, p. 587 ff.).

The acyl halides of the formula (VI), carboxylic anhydrides of theformula (VII), chloroformic esters or chloroformic thioesters of theformula (VIII), chloromonothioformic esters or chlorodithioformic estersof the formula (IX), sulphonyl chlorides of the formula (X), phosphoruscompounds of the formula (XI) and metal hydroxides, metal alkoxides oramines of the formulae (XII) and (XIII) and isocyanates of the formula(XIV) and carbamoyl chlorides of the formula (XV) furthermore requiredas starting materials for carrying out the processes (C), (D), (E), (F),(G), (H) and (I) according to the invention are generally knowncompounds of organic or inorganic chemistry.

The process (A) is characterized in that compounds of the formula (II)in which A, B, Q¹, Q², W, X, Y, Z and R⁸ are each as defined above aresubjected to an intramolecular condensation in the presence of a base.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metals and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium, oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). It is furthermore possible to usealkali metals such as sodium or potassium. Also suitable are alkalimetal and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and furthermore also alkalimetal alkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in about double equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

Suitable catalysts for carrying out the processes B (α) to B (γ)according to the invention are palladium(0) complexes. Use is made, forexample, of tetrakis(tri-phenylphosphine)palladium. Also suitable arepalladium(II) compounds, such as bis(triphenylphosphine)palladium(II)chloride.

Suitable acid acceptors for carrying out the processes B (α) and B (γ)according to the invention are inorganic or organic bases. Thesepreferably include alkaline earth metal or alkali metal hydroxides,acetates, carbonates or bicarbonates, such as, for example, sodiumhydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide,sodium acetate, potassium acetate, calcium acetate or ammonium acetate,sodium carbonate, potassium carbonate or ammonium carbonate, sodiumbicarbonate or potassium bicarbonate, alkali metal fluorides, such as,for example, potassium fluoride or caesium fluoride, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

Suitable diluents for carrying out the process B (γ) according to theinvention are water, organic solvents and any mixtures thereof. Examplesof organic solvents suitable for processes B (α) to B (γ) are:aliphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, methylene chloride,chloroform, carbon tetrachloride, dichloroethane, trichloroethane ortetra-chloroethylene; ethers, such as diethyl ether, diisopropyl ether,methyl tert-butyl ether, methyl tert-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethyleneglycol dimethyl ether or anisole; alcohols, such as methanol, ethanol,n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether; diethylene glycol monoethyl ether; water.

The reaction temperature in process (B) according to the invention canbe varied within a relatively wide range. In general, the process iscarried out at temperatures between 0° C. and +180° C., preferablybetween 50° C. and +150° C.

When carrying out the process B (α), silylacetylenes of the formula(III) and compounds of the formulae (I-a′) to (I-g′) are employed in amolar ratio of from 1:1 to 10:1, preferably from 1:1 to 3:1. Whencarrying out the process B(β), vinylstannanes of the formula (IV) andcompounds of the formulae (I-a′) to (I-g′) are employed in a molar ratioof from 1:1 to 10:1, preferably from 1:1 to 3:1.

When carrying out the process B (γ) according to the invention, boronicacids of the formula (V) and compounds of the formulae (I-a′) and (I-g′)are employed in a molar ratio of from 1:1 to 3:1, preferably from 1:1 to2:1.

The catalyst is generally employed in amounts of from 0.005 to 0.5 mol,preferably from 0.01 to 0.1 mol, per mole of the compounds (I-a′) to(I-g′). The base is generally employed in excess.

The process (C-α) is characterized in that compounds of the formula(I-a) are in each case reacted with carbonyl halides of the formula(VI), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

Suitable diluents for use in the process (C-α) according to theinvention are all solvents which are inert to the acyl halides.Preference is given to using hydrocarbons, such as benzene, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetra-hydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, nitriles, such as acetonitrile, and also strongly polarsolvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.The hydrolytic stability of the acyl halide permitting, the reaction canalso be carried out in the presence of water.

Suitable acid binders for the reaction according to the process (C-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabi-cycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal carbonates and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

The reaction temperatures in the process (C-α) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C-α) according to the invention, thestarting materials of the formula (I-a) and the carbonyl halide of theformula (VI) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of carbonyl halide. Work-up is carried out by customarymethods.

The process (C-β) is characterized in that compounds of the formula(I-a) are reacted with carboxylic anhydrides of the formula (VII), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (C-β) according to theinvention are preferably those diluents which are also preferred whenusing acyl halides. Furthermore, it is also possible for excesscarboxylic anhydride to act simultaneously as diluent.

Suitable acid binders for process (C-β), which are added, ifappropriate, are preferably those acid binders which are also preferredwhen using acyl halides.

The reaction temperatures in the process (C-β) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (C-β) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (VII) are generally each employed in approximatelyequivalent amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of carboxylic anhydride. Work-up is carriedout by customary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

The process (D) is characterized in that compounds of the formula (I-a)are in each case reacted with chloroformic esters or chloroformicthioesters of the formula (VIII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

Acid binders suitable for the reaction according to process (D)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for use in the process (D) according to the inventionare all solvents which are inert to the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzene, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, nitriles, such as acetonitrile, and alsostrongly polar solvents, such as dimethylformamide, dimethyl sulphoxideand sulpholane.

When carrying out the process (D) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe reaction is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (D) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (D) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (VIII) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed, and the reaction mixture that remains isconcentrated by removing the diluent under reduced pressure.

The process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with compoundsof the formula (IX) in the presence of a diluent and, if appropriate, inthe presence of an acid binder.

In preparation process (E), about 1 mol of chloromonothioformic ester orchlorodithioformic ester of the formula (IX) are employed per mole ofstarting material of the formula (I-a), at from 0 to 120° C., preferablyfrom 20 to 60° C.

Suitable diluents, which are added, if appropriate, are all inert polarorganic solvents, such as nitrites, ethers, esters, amides, sulphones,sulphoxides, but also halogenoalkanes.

Preference is giving to using acetonitrile, ethyl acetate, dimethylsulphoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders can be dispensed with.

If acid binders are used, these can be customary inorganic or organicbases, examples that may be mentioned being sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with sulphonylchlorides of the formula (X), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (F), about 1 mol of sulphonyl chloride of theformula (X) is used per mole of starting material of the formula, atfrom −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents, which are added, if appropriate, are all inert polarorganic solvents, such as esters, ethers, amides, nitrites, sulphones,sulphoxides, or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using acetonitrile, ethyl acetate, dimethylsulphoxide, tetrahydrofuran, dimethylformamide of methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders can be dispensed with.

If acid binders are used, these can be customary inorganic or organicbases, examples which may be mentioned being sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (G) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with phosphoruscompounds of the formula (XI), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (G), from 1 to 2, preferably from 1 to 1.3, molof the phosphorus compound of the formula (XI) are used per mole of thecompound (I-a), at temperatures between −40° C. and 150° C., preferablybetween −10 and 110° C., to give compounds of the formula (I-e).

Suitable diluents which may be added, if appropriate, are all inertpolar organic solvents, such as ethers, amides, nitriles, alcohols,sulphides, sulphones, sulphoxides. etc.

Preference is given of using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

Suitable acid binders, which may be added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Examples which may be mentioned are sodium hydroxide, sodium carbonate,potassium carbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Thepurification of the resulting end product is preferably carried out bycrystallization, chromatographic purification or by so-called “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

The process (H) is characterized in that compounds of the formula (I-a)are reacted with metal hydroxides or metal alkoxides of the formula(XII) or amines of the formula (XIII), if appropriate in the presence ofa diluent.

Preferred diluents for the process (H) according to the invention areethers, such as tetrahydrofuran, dioxane or diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.

The process (H) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (I) according to the invention is characterized in that(I-α) compounds of the formula (I-a) are in each case reacted withcompounds of the formula (XIV), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (I-β) withcompounds of the formula (XV), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (I-α), about 1 mol of isocyanate of the formula(XIV) is used per mole of starting material of the formula (I-a), atfrom 0 to 100° C., preferably at from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as nitrites, esters, ethers, amides, sulphones andsulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Particularly advantageous catalysts are organotin compounds, such as,for example, dibutyltin dilaurate. The process is preferably carried outat atmospheric pressure.

In preparation process (I-β), about 1 mol of carbamoyl chloride of theformula (XV) is used per mole of starting material of the formula (I-a),at from −20 to 150° C., preferably at from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as nitrites, esters, ethers, amides, sulphones,sulphoxides, or halogenated hydrocarbons.

Preference is given to using acetonitrile, ethyl acetate, dimethylsulphoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders can be dispensed with.

If acid binders are used, these can be customary inorganic or organicbases, examples which may be mentioned being sodium hydroxide, sodiumcarbonate, potassium carbonate, triethylamine and pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

Suitable diluents for carrying out the process (J) according to theinvention are all customary organic solvents which are inert towards thereactants. Preference is given to using hydrocarbons, such aso-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers,such as dibutyl ether, glycol dimethyl ether and diglycol dimethylether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide or N-methylpyrrolidone. Suitable cosolvents accordingto Example (I-2-a) are alcohols, such as methanol, ethanol, propanol orbutanol, but also water.

Suitable acid acceptors for carrying out the process (J) according tothe invention are all customary acid binders. Preference is giving tousing tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base or N,N-dimethylaniline.

When carrying out the process (J) according to the invention, thereaction temperatures can be varied within a relatively wide range. Theprocess is expediently carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 220° C.

The process (J) according to the invention is preferably carried outunder atmospheric pressure.

When carrying out the process (J) according to the invention, in generalan equimolar amount of the ketene derivative of the formula (XVII) andif appropriate also an equimolar amount of acid acceptor are used permole of silyl ether of the formula (XVI). However, it is also possibleto use a relatively large excess (up to 5 mol) of one component or theother.

The 5,6-dihydro-pyrones of the formula (I) according to the inventionhave very good pesticidal activity and are highly compatible with cropplants.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes found in agriculture, inforests, in the protection of stored products and materials and in thehygiene sector, and they are tolerated well by plants and havefavourable homeotherm toxicity. They are preferably employed as cropprotection agents. They are active against normally sensitive andresistant species, and against all or individual developmental stages.The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus,Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp.,Schistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp.,Damalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, PlutelIa xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis,Ceratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The plant-parasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

At certain concentrations or application rates, the compounds accordingto the invention can, if appropriate, also be employed as herbicides andmicrobicides, for example as fungicides, antimycotics and bactericides.If appropriate, they can also be used as intermediates or precursors forthe synthesis of further active compounds.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to useorganic solvents as cosolvents. The following are essentially suitableas liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic materials such as highly-disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam formers are: for example nonionic and anionic emulsifierssuch as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, or else protein hydrolysates; suitabledispersants are: for example lignin-sulphite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms.

Examples of particularly advantageous mixing components are thefollowing:

Fungicides

-   aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine,    azaconazole, azoxystrobin,-   benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,    bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,    bromuconazole, bupirimate, buthiobate,-   calcium polysulphide, capsimycin, captafol, captan, carbendazim,    carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,    chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,    cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,-   debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,    dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,    diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,    ditalimfos, dithianon, dodemorph, dodine, drazoxolon,-   edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,-   famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,    fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,    fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover,    fluoromide, fluquinconazole, flurprimidol, flusilazole,    flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium,    fosetyl-sodium, fthalide, fuberidazole, furalaxyl, furametpyr,    furcarbonil, furconazole, furconazole-cis, furmecyclox,-   guazatine,-   hexachlorobenzene, hexaconazole, hymexazole,-   imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,    iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),    iprodione, irumamycin, isoprothiolane, isovaledione,-   kasugamycin, kresoxim-methyl, copper preparations, such as: copper    hydroxide, copper naphthenate, copper oxychloride, copper sulphate,    copper oxide, oxine-copper and Bordeaux mixture,-   mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,    metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,    metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,-   nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,-   ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,    oxyfenthiin,-   paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,    picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim,    probenazole, prochloraz, procymidone, propamocarb,    propanosine-sodium, propiconazole, propineb, pyraclostrobin,    pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,-   quinconazole, quintozene (PCNB),-   sulphur and sulphur preparations,-   tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,    thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,    tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,    triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,    trifloxystrobin, triflumizole, triforine, triticonazole,-   uniconazole,-   validamycin A, vinclozolin, viniconazole,-   zarilamide, zineb, ziram and also-   Dagger G,-   OK-8705,-   OK-8801,-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,-   (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,-   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,-   1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone    O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropane-carboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole.-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(bromomethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol (OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propinyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,-   8-hydroxyquinoline sulphate,-   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride,-   ethyl [(4-chlorophenyl)-azo]-cyanoacetate,-   potassium hydrogen carbonate,-   methanetetrathiol sodium salt,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,-   N-formyl-N-hydroxy-DL-alanine sodium salt,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[3,4-dimethoxyphenyl-3-(4-fluorophenyl)-acryloxy]-morpholine.

Bactericides

-   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.

Insecticides/Acaricides/Nematicides

-   abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,    aldoxycarb, alpha-cypernethrin, alphamethrin, amitraz, avermectin,    AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphos M,    azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,    bifenazate, bifenthrin, bioethanomethrin, biopermethrin,    bistrifluorone, BPMC, bromophos A, bufencarb, buprofezin,    butathiofos, butocarboxim, butylpyridaben,-   cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,    cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,    chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,    chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,    clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,    cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,    cypermethrin, cyromazine,-   deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,    diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,    dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,-   eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,    esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,    etoxazole, etrimfos,-   fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,    fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,    fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,    fluazuron, flubrocythrinate, flucycloxuron, flucythrinate,    flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophos,    fosmethilan, fosthiazate, fubfenprox, furathiocarb,-   granulosis viruses,-   halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,    hydroprene,-   imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,    ivermectin,-   lambda-cyhalothrin, lufenuron,-   malathion, mecarbam, metaldehyde, methamidophos, Metharhizium    anisopliae, Metharhizium flavoviride, methidathion, methiocarb,    methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,    mevinphos, milbemectin, rilbemycin, monocrotophos,-   naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosis    viruses,-   omethoat, oxamyl, oxydemethon M,-   Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,    propargite, propoxur, prothiofos, prothoate, pymetrozine,    pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyridathion,    pyrimidifen, pyriproxyfen,-   quinalphos,-   ribavirin,-   salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,    sulprofos,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,    tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,    thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,    thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,    triarathene, triazamate, triazophos, triazuron, trichlophenidine,    trichlorfon, triflumuron, trimethacarb,-   vamidothion, vaniliprole, Verticillium lecanii,-   YI 5302,-   zeta-cypermethrin, zolaprofos-   (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropane    carboxylate-   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropane carboxylate-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole-   2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide-   3-methylphenyl propylcarbamate-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone-   Bacillus thuringiensis strain EG-2348-   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde-   ethyl    [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.-   N-cyanomethyl-4-trifluoromethyl-nicotinamide-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethyl-pyridin-2-yloxy)-propoxy]-benzene.

Mixtures with other known active compounds such as herbicides or withfertilizers and growth regulators are also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergist added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms. When used against hygiene pests and stored-product pests, theactive compound is distinguished by an excellent residual action on woodand clay as well as good stability to alkali on limed substrates.

The active compounds according to the invention are not only activeagainst plant pests, hygiene pests and stored-product pests, but also,in the veterinary medicine sector, against animal parasites(ectoparasites) such as hard ticks, soft ticks, mange mites, harvestmites, flies (stinging and licking), parasitizing fly larvae, lice, hairlice, bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order Diptera and the suborders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstmongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds according to the invention are also suitable forcontrolling arthropods which attack agricultural livestock such as, forexample, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes,rabbits, chickens, turkeys, ducks, geese, honey-bees, other domesticanimals such as, for example, dogs, cats, caged birds, aquarium fish andso-called experimental animals such as, for example, hamsters, guineapigs, rats and mice. By controlling these arthropods, cases of death andreductions in productivity (for meat, milk, wool, hides, eggs, honey andthe like) should be diminished, so that more economical and simpleranimal husbandry is possible by the use of the active compoundsaccording to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration such as, for example, by injections (intramuscularly,subcutaneously, intravenously, intraperitoneally and the like),implants, by nasal administration, by dermal administration in the formof, for example, immersing or dipping, spraying, pouring-on,spotting-on, washing, dusting, and with the aid ofactive-compound-comprising moulded articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

When used for cattle, poultry, domestic animals and the like, the activecompounds can be applied as formulations (for example powders,emulsions, flowables) comprising the active compounds in an amount of 1to 80% by weight, either directly or after 100- to 10 000-fold dilution,or they may be used as a chemical dip.

Moreover, it has been found that the active compounds according to theinvention show a potent insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned by way of example and withpreference, but not by way of limitation:

Beetles such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

Dermapterans such as

-   Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus    augur.

Termites such as

-   Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,    Reticulitermes flavipes, Reticulitermes santonensis. Reticulitermes    lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,    Coptotermes formosanus.

Bristle-tails such as Lepisma saccharina.

Industrial materials in the present context are understood as meaningnon-living materials such as, preferably, polymers, adhesives, glues,paper and board, leather, wood, timber products and paints.

The materials which are to be protected from insect attack is veryespecially preferably wood and timber products.

Wood and timber products which can be protected by the compositionaccording to the invention, or mixtures comprising it, are to beunderstood as meaning, for example:

construction timber, wooden beams, railway sleepers, bridge components,jetties, vehicles made of wood, boxes, pallets, containers, telephonepoles, wood lagging, windows and doors made of wood, plywood, chipboard,joinery, or timber products which quite generally are used in houseconstruction or building joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations such as powders, granules, solutions,suspensions, emulsions or pastes.

The abovementioned formulations can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellant, if desired desiccants and UV stabilizers, and if desiredcolorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for protecting woodand timber products comprise the active compound according to theinvention in a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

The amount of composition or concentrate employed depends on the speciesand the abundance of the insects and on the medium. The optimal quantityto be employed can be determined in each case by test series uponapplication. In general, however, it will suffice to employ 0.0001 to20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

A suitable solvent and/or diluent is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetter.

Organochemical solvents which are preferably employed are oily oroil-type solvents with an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Such oily and oil-typesolvents which are insoluble in water and of low volatility and whichare used are suitable mineral oils or their aromatic fractions ormineral-oil-containing solvent mixtures, preferably white spirit,petroleum and/or alkylbenzene.

Mineral oils with a boiling range of 170 to 220° C., white spirit with aboiling range of 170 to 220° C., spindle oil with a boiling range of 250to 350° C., petroleum and aromatics with a boiling range of 160 to 280°C., oil of terpentine, and the like are advantageously used.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene are used.

The organic oily or oil-type solvents of low volatility and with anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide-fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, some of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Aliphatic organochemical solvents which containhydroxyl and/or ester and/or ether groups are preferably used, such as,for example, glycol ethers, esters or the like.

Organochemical binders used for the purposes of the present inventionare the synthetic resins and/or binding drying oils which are known perse and which can be diluted in water and/or dissolved or dispersed oremulsified in the organochemical solvents employed, in particularbinders composed of, or comprising, an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenol resin, hydrocarbon resin such as indene/coumarone resin,silicone resin, drying vegetable and/or drying oils and/or physicallydrying binders based on a natural and/or synthetic resin.

The synthetic resin employed as binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances mayalso be used as binders, in amounts of up to 10% by weight. In addition,colorants, pigments, water repellants, odour-masking agents, andinhibitors or anticorrosive agents and the like, all of which are knownper se, can be employed.

In accordance with the invention, the composition or the concentratepreferably comprises, as organochemical binders, at least one alkydresin or modified alkyd resin and/or a drying vegetable oil. Alkydresins which are preferably used in accordance with the invention arethose with an oil content of over 45% by weight, preferably 50 to 68% byweight.

Some or all of the abovementioned binder can be replaced by a fixative(mixture) or plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds, and also crystallizationor precipitation. They preferably replace 0.01 to 30% of the binder(based on 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate,phosphoric esters such as tributyl phosphate, adipic esters such asdi-(2-ethylhexyl)-adipate, stearates such as butyl stearate or amylstearate, oleates such as butyl oleate, glycerol ethers orhigher-molecular-weight glycol ethers, glycerol esters andp-toluenesulphonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, forexample, polyvinyl methyl ether, or ketones such as benzophenone andethylenebenzophenone.

Other suitable solvents or diluents are, in particular, water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective timber protection is achieved by industrial-scaleimpregnating processes, for example the vacuum, double-vacuum orpressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing components are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozideand triflumuron,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The combinations according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., fouling by sessile Entomostraka groups, which come under thegeneric term Cirripedia (cirriped crustaceans), is of particularimportance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the combinations according to the invention, alone or incombination with other active compounds, allows the use of heavy metalssuch as, for example, in bis(trialkyltin) sulphides, tri-n-butyltinlaurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combinations with the antifoulingcompositions according to the invention are:

algicides such as

-   2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,    dichlorophen, diuron, endothal, fentin acetate, isoproturon,    methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as

-   benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,    dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,    tolylfluanid and azoles such as azaconazole, cyproconazole,    epoxyconazole, hexaconazole, metconazole, propiconazole and    tebuconazole;

molluscicides such as

-   fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb and    trimethacarb;

or conventional antifouling active compounds such as

-   4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl    sulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl,    potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,    pyridine-triphenylborane, tetrabutyldistannoxane,    2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,    2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide    and 2,4,6-trichlorophenylmaleiimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compositions according to the invention in aconcentration of 0.001 to 50% by weight, in particular 0.01 to 20% byweight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds according to the invention, antifoulingpaints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active compounds and excipients in domestic insecticide productsfor controlling these pests. They are active against sensitive andresistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxyscalcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenoccphalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponlotus herculcanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

They are used as aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutiloin, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds according to the invention have strong herbicidal activityand a broad active spectrum when used on the soil and on above-groundparts of plants. To a certain extent they are also suitable for theselective control of monocotyledonous and dicotyledonous weeds inmonocotyledonous and dicotyledonous crops, both by the pre-emergence andby the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the cultivars protectable or not protectable byplant breeders' rights. Plant parts are to be understood as meaning allparts and organs of plants above and below the ground, such as shoot,leaf, flower and root, examples which may be mentioned being leaves,needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots,tubers and rhizomes. The plant parts also include harvested material,and vegetative and generative propagation material, for examplecuttings, tubers, rhizomes, offsets and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and cultivars, or those obtained by conventional biologicalbreeding, such as crossing or protoplast fusion, and parts thereof, aretreated. In a further preferred embodiment, transgenic plants andcultivars obtained by genetical engineering, if appropriate incombination with conventional methods (Genetically Modified Organisms),and parts thereof are treated. The term “parts” or “parts of plants” or“plant parts” has been explained above.

Particularly preferably, plants of the cultivars which are in each casecommercially available or in use are treated according to the invention.Cultivars are to be understood as meaning plants having certainproperties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can bevarieties, bio- or genotypes.

Depending on the plant species or cultivars, their location and growthconditions (soils, climate, vegetation period, diet), the treatmentaccording to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or cultivars (i.e. those obtained by geneticalengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds, forexample imidazolinones, sulphonylureas, glyphosate or phosphinotricin(for example the “PAT” gene). The genes which impart the desired traitsin question can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula (I).The preferred ranges stated above for the active compounds also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the mixtures specifically mentioned in thepresent text.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to useorganic solvents as cosolvents. The following are essentially suitableas liquid solvents: aromatics such as xylene, toluene oralkylnhaplhthalenies, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as highly-disperse silica, alumina and silicates;suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, or else synthetic granules of inorganic and organic meals,and granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks; suitable emulsifiers and/or foam formers are:for example nonionic and anionic emulsifiers such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates, or else protein hydrolysates; suitable dispersants are:for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchalizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95%. by weight ofactive compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for exampleacetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, BAS-662H, beflubutamid,benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazon,benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl),bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim,bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chloitoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet,mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, naproparide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham,picolinafen, piperophos, pretilachlor, primisulfuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example I-a-1

5.6 g (50 mmol) of potassium tert-butoxide are initially charged in 30ml of absolute DMF and, at 60° C., admixed with 10.6 g of the compoundaccording to Example II-8 in 20 ml of DMF. The reaction solution isstirred at 60° C. for 3 hours, poured into ice-water and acidified withconcentrated hydrochloric acid. The precipitate is filtered off withsuction, washed and dried.

Yield: 7.4 g (77% of theory), m.p. >220° C.

Example I-a-2

9.8 g (44 mmol) of 2,4,5-trimethylphenyl chlorocarbonyl ketene areinitially charged in 80 ml of anhydrous xylene and, at 20° C., 8.1 g (44mmol) of trimethylsityloxy-methylidenecyclohexane in 30 ml of anhydrousxylene are added dropwise with exclusion of moisture. The mixture isheated at reflux for 8 hours, 7.3 ml of methanol are then added, andheating at reflux is continued for another 2 hours. The mixture iswashed with water and saturated sodium chloride solution and dried oversodium sulphate. The mixture is concentrated under reduced pressure andthe residue is chromatographed on silica gel (35 to 70 μm) usingtoluene/acetone (20:1).

Yield: 3.9 g (^ 27% of theory). m.p. 174-175° C.

Example I-a-3

9.4 g (42.2 mmol) of 2,4,5-trimethylphenyl chlorocarbonyl ketene areinitially charged in 80 ml of anhydrous xylene and, at 20° C., 7.1 g(42.2 mmol) of trimethylsilyloxymethylidenecyclopentane in 30 ml ofanhydrous xylene are added dropwise with exclusion of moisture. Themixture is heated at reflux for 8 hours and then washed with water andsaturated sodium chloride solution, and the organic phase is dried oversodium sulphate. The organic phase is evaporated and the residue ischromatographed on silica gel (35 to 70 μm) using the mobile phasetoluene.

Yield: 3.2 g (^ 25% of theory). m.p. 122-124° C.

The following compounds of the formula I-a are obtained analogously toExamples I-a-1, I-a-2 and I-a-3 and in accordance with the generalstatements on the preparation

(I-a)

Ex. No. W X Y Z B A Q¹ Q² m.p. ° C. I-a-4 H CH₃ 4-Cl H CH₃ CH₃ OCH₃ H164-166 I-a-5 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H wax I-a-6 H CH₃5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ 125 I-a-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃CH₃ 140 I-a-8 H CH₃ 5-CH₃ H CH₃ CH₃ OCH₃ H oil I-a-9 CH₃ CH₃ 3-CH₃ 4-CH₃CH₃ CH₃ OCH₃ H 121-122 I-a-10 CH₃ CH₃ 3-CH₃ 4-CH₃ CH₃ CH₃ OH H 184-186I-a-11 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H 115-117 I-a-12 CH₃ CH₃ 4-CH₃ H

H 171 I-a-13 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ H H 174 I-a-14 CH₃ CH₃4-CH₃ H CH₃ CH₃ OC₂H₅ H  90-93 I-a-15 CH₃ CH₃ 4-CH₃ H —(CH₂)₅— OC₂H₅ H148-150 I-a-16 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OC₃H₇ H 108-110 I-a-17 CH₃ CH₃4-CH₃ H CH₃ C₂H₅ OCH₃ H 111-113 I-a-18 CH₃ CH₃ 4-CH₃ H C₂H₅ C₂H₅ OCH₃ H123-125 I-a-19 CH₃ CH₃ 4-CH₃ H —(CH₂)₅— OH H 154-156 I-a-20 H CH₃5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ oil I-a-21 H CH₃ 5-(4-Cl—C₆H₄₎ 4-CH₃ CH₃CH₃ CH₃ CH₃ 182-184° C. I-a-22 CH₃ CH₃ 5-(4-Cl—C₆H₄₎ 4-CH₃ CH₃ CH₃ CH₃CH₃ 233-234° C. I-a-23 H CH₃ 5-Br H CH₃ CH₃ CH₃ CH₃ 184-186° C. I-a-24 HCH₃ 5-(3,5-Cl₂—C₆H₃) H CH₃ CH₃ CH₃ CH₃ 192-193° C. I-a-25 H CH₃5-(2-CH₃, 4-Cl— H CH₃ CH₃ CH₃ CH₃ 202-203° C. C₆H₃) I-a-26 H CF₃ 4-Cl HCH₃ CH₃ CH₃ CH₃ 185-186° C. I-a-27 Br C₃H₇ 4-Br H CH₃ CH₃ CH₃ CH₃ oilI-a-28 C₂H₅ C₂H₅ 4-Br H CH₃ CH₃ CH₃ CH₃ 178-180° C. I-a-29 Cl Cl 4-CF₃ HCH₃ CH₃ CH₃ CH₃ 233-234° C. I-a-30 Cl Cl 4-Cl H CH₃ CH₃ CH₃ CH₃ >250° C.I-a-31 H Cl 5-(4-Cl—C₆H₄₎ H CH₃ CH₃ CH₃ CH₃ 204-205° C.

Example I-A-b-1

1.5 g (3.9 mmol) of the compound according to Example I-a-1 areinitially charged in 15 ml of anhydrous dichloromethane and admixed with0.78 ml (5.85 mmol) of triethylamine. At 0° C., 0.57 g (5.07 mmol) ofisobutyryl chloride are added, and the mixture is stilled at roomtemperature for 2 hours. The reaction solution is extracted with 10%strength citric acid and washed with dichloromethane. The mixture isthen extracted with 1 N NaOH and washed once more with dichloromethaneand dried, and the solvent is evaporated.

Yield: 1.2 g (^ 68% of theory).

¹H-NMR (400 MHz, DMSO): δ=0.69 (d, 6H, (CH ₃)₂—CH); 1.17 (s, 6H,(CH₃)₂—C), 1.52 (s, 6H, (CH₃)₂—C—O), 2.11 (s, 6H, 2 Ar—CH₃) ppm.

The following compounds of the formulae (I-A-b) and (I-B-b) are obtainedanalogously to Examples (I-A-b-1) and in accordance with the generalstatements on the preparation

(I-A-b)

(I-B-b)

Ex. No. W X Y Z B A Q¹ Q² R¹ m.p. ° C. I-A-b-2 H CH₃ 5-CH₃ H CH₃ CH₃OCH₃ H CH₃ oil I-A-b-3 H CH₃ 4-Cl H CH₃ CH₃ OCH₃ H CH₃ oil I-A-b-4 CH₃CH₃ 4-CH₃ H

H CH(CH₃)₂ 84-86 I-A-b-5 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H CH₃ 118-120I-A-b-6 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

115-117 I-A-b-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

oil I-A-b-8 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ O—COCH₃ H CH₃ 125-127 I-A-b-9 CH₃CH₃ 4-CH₃ H —(CH₂)₄— O—COCH₃ H CH₃ 122-124 I-A-b-10 H CH₃ 5-(4-Cl—C₆H₄)H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ oil I-A-b-11 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ HH i-C₃H₇ oil I-B-b-12 H CH₃ 5-CH₃ H CH₃ CH₃ OCH₃ H CH₃ oil I-B-b-13 HCH₃ 4-Cl H CH₃ CH₃ OCH₃ H CH₃ oil I-B-b-14 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃H CH₃ 110-113 I-B-b-15 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

134-136 I-B-b-16 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ oil I-B-b-17 CH₃CH₃ 4-CH₃ H CH₃ CH₃ H H i-C₃H₇ 88-91 I-A-b-18 H CH₃ 5-(4-Cl—C₆H₄) H CH₃CH₃ H H i-C₃H₇ oil

Isomer mixtures of the formulae I-A-b and I-B-b were separated by silicagel column chromatography.

Example I-A-c-1

1.5 g (3.9 mmol) of the compound according to Example I-a-1 areinitially charged in 15 ml of anhydrous dichloromethane and admixed with0.78 ml (5.85 mmol) of triethylamine. At 0° C., 0.63 g (5.07 mmol) ofisopropyl chloroformate are added, and the mixture is stirred at roomtemperature for 2 hours. The reaction solution is extracted with 10%strength citric acid and washed with dichlorometlhane. The mixture isthen extracted with 1 N NaOH and washed once more with dichloromethaneand dried, and the solvent is evaporated.

Yield: 1.2 g (^ 65% of theory).

¹H-NMR (400 MHz, DMSO): δ=1.08 (d, 6H, (CH ₃)₂—CH); 1.16 (s, 6H,(CH₃)₂—C), 2.11 (s, 6H, 2 Ar—CH₃), 7.36 (s, 2H, 2 Ar—H) ppm.

The following compounds of the formulae (I-A-c) and (I-B-c) wereobtained analogously to Example I-A-c-1 and in accordance with thegeneral statements on the preparation

(I-A-c)

(I-B-c)

Ex. No. W X Y Z B A Q¹ Q² M R² m.p. ° C. I-A-c-2 CH₃ CH₃ 4-CH₃ H CH₃ CH₃OCH₃ H O CH₃ 108-110 I-A-c-3 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ Oi-C₃H₇ oil I-A-c-4 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ H H O i-C₃H₇ oilI-B-c-1 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ H H O i-C₃H₇ oil I-B-c-2 CH₃ CH₃ 4-CH₃ H

H O i-C₃H₇ oil I-B-c-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ H H O i-C₃H₇ oil I-A-c-8H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H O C₂H₅ oil I-A-c-9 H CH₃ 5-(4-Cl—C₆H₄)H CH₃ CH₃ CH₃ CH₃ O C₂H₅ 144 I-A-c-10 H CH₃ 5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃CH₃ CH₃ O C₂H₅ oil I-A-c-11 H CH₃ 5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ O C₂H₅I-A-c-12 H CH₃ 5-Br H CH₃ CH₃ CH₃ CH₃ O C₂H₅ oil

Example II-1

Preparation of the Acyl Chloride:

9.0 g (34.5 mmol) of 2-methyl-5-(4-chlorophenyl)-phenylacetic acid areinitially charged in 50 ml of anhydrous toluene and 2 drops of DMF, and6.15 g (51.8 mmol; 3.74 ml) of thionyl chloride are added. The mixtureis stirred at 100° C. until evolution of gas has ceased. The solvent isdistilled off.

6.00 g (34.5 mmol) of ethyl 3-hydroxy-2,2,3-trimethyl-butyrate and 10.3g (34.5 mmol) of acyl chloride in 40 ml of anhydrous toluene are boiledat reflux overnight. The solvent is then distilled off and the reactionmixture is purified by silica gel column chromatography (petroleumether:ethyl acetate. 3:1•1:1).

Yield: 11.6 g (^ 80.6% of theory).

¹H-NMR (DMSO, 400 MHz): δ=1.06 (s, 6H, 2CH₃), 1.12 (t, 3H, CO₂CH₂CH ₃),1.50 (s, 6H, 2CH₃), 2.26 (s, 3H, Ar—CH₃), 3.66 (s, 2H, CH₂), 4.00 (q,2H, CO₂CH ₂CH₃) ppm.

The following compounds of the formula (II) are obtained analogously toExample II-1 and in accordance with the general statements on thepreparation

(II)

Ex. No. W X Y Z B A Q¹ Q² R⁸ m.p. ° C. II-2 CH₃ CH₃ 4-CH₃ H

H C₂H₅ oil II-3 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-4 CH₃ CH₃4-CH₃ H CH₃ CH₃ H H CH₃ oil II-5 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H CH₃oil II-6 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-7 CH₃ CH₃4-(4-Cl—C₆H₄) H CH₃ CH₃ H H CH₃ oil II-8 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃CH₃ CH₃ C₂H₅ oil II-9 H CH₃ 5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅ oilII-10 H CH₃ 5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-11 CH₃ CH₃5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-12 H CH₃ 5-Br H CH₃ CH₃CH₃ CH₃ C₂H₅ oil II-13 H CH₃ 5- H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil(3,5-Cl₂—C₆H₃) II-14 H CF₃ 4-Cl H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-15 Br C₃H₇4-Br H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-16 C₂H₅ C₂H₅ 4-Br H CH₃ CH₃ CH₃ CH₃C₂H₅ oil II-17 Cl Cl 4-CF₃ H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-18 Cl Cl 4-Cl HCH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-19 H Cl 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅oil

The compounds were obtained as oils and used without furtherpurification for preparing compounds of the formula (I-a).

USE EXAMPLES Example A

Meloidogyne Test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

After the desired period of time, the nematicidal action in % isdetermined using the formation of galls as a measure. 100% means that nogalls have been found; 0% means that the number of galls on the treatedplants corresponds to that on the untreated control.

In this test, for example, the following compounds of the PreparationExamples exhibit good activity.

TABLE A Plant-damaging nematodes Meloidogyne test Active compound Killrate in % after Active compounds concentration in ppm 14^(d) Ex. I-a-520 100 Ex. I-B-b-17 20 90 Ex. I-B-c-1 20 90 Ex. I-A-b-4 20 90 Ex.I-B-c-2 20 100 Ex. I-A-b-10 20 100 Ex. I-A-b-1 20 100

Example B

Myzus Test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thepeach aphid (Myzus persicae) are treated by being dipped into apreparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all of the aphids have been killed: 0% means that none of theaphids has been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity.

TABLE B Plant-damaging insects Myzus test Active compound Kill rate in %after Active compounds concentration in ppm 6^(d) Ex. I-a-5 1000 95 Ex.I-a-7 1000 90 Ex. I-a-6 1000 95

Example C

Panonychus Test

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Plum trees (Prunus domestica), of a height of approximately 30 cm, whichare heavily infested by all stages of the fruit tree red spider mite(Panonychus ulmi) are sprayed with a preparation of active compound ofthe desired concentration.

After the desired period of time, the effect in % is determined. 100%means that all of the spider mites have been killed: 0% means that noneof the spider mites has been killed.

In this test, for example, the following compound of the PreparationExamples shows good activity.

TABLE C Plant-damaging mites Panonychus test Active compound Kill ratein % after Active compounds concentration in ppm 14^(d) Ex. I-a-6 200100

Example D

Phaedon larvae Test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all of the beetle larvae have been killed. 0% means that noneof the beetle larvae has been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity.

TABLE D Plant-damaging insects Phaedon larvae test Active compound Killrate in % after Active compounds concentration in ppm 7^(d) Ex. I-a-51000 100 Ex. I-a-6 1000 100 Ex. I-A-b-10 1000 100 Ex. I-A-c-3 1000 90Ex. I-a-13 1000 100 Ex. I-a-1 1000 100 Ex. I-A-b-11 1000 100

Example E

Spodoptera frugiperda Test

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all of the caterpillars have been killed; 0%. means that noneof the caterpillars has been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity.

TABLE E Plant-damaging insects Spodoptera frugiperda test Activecompound Kill rate in % after Active compounds concentration in ppm7^(d) Ex. I-a-6 1000 100 Ex. I-A-b-10 1000 100

Example F

Tetranychus Test (OP-Resistant/Dip Treatment)

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all of the spider mites have been killed, 0% means that noneof the spider mites has been killed.

In this test, for example, the following compounds of the PreparationExamples show an activity which is superior to the prior art.

In this test, for example, the following compounds of the PreparationExamples show good activity.

TABLE F Plant-damaging mites Tetranychus test (OP-resistant/diptreatment) Active compound Kill rate in % after Active compoundsconcentration in ppm 7^(d) Ex. I-a-6 100 100 Ex. I-B-b-17 100 100 Ex.I-B-c-1 100 100 Ex. I-B-c-2 100 99 Ex. I-B-b-16 100 100 Ex. I-A-c-3 0.01100

Example G

Meloidogyne Test

Solvent: 8 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Containers are filled with sand, solution of active compound.Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

After the desired period of time, the nematicidal action in % isdetermined using the formation of galls as a measure. 100% means that nogalls have been found; 0% means that the number of galls on the treatedplants corresponds to that on the untreated control.

Active compounds, application rates and results are shown in the tablebelow:

TABLE G Nematicides Meloidogyne incoginita Kill rate in % at activeActive compound compound concentration in ppm Ex. I-a-7 20 ppm = 100%

Example H

Sphaerotheca Test (Cucumber)/Protective

Solvent: 48.8 parts by weight of N,N-dimethylformamide

Emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young cucumber plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Sphaerotheca fuliginea. The plants are then placed in a greenhouse at70% relative atmospheric humidity and a temperature of 23° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% meais that no infection is observed.

TABLE H Sphaerotheca test (cucumber)/protective Application rate ofactive compound Active compound in g/ha Efficacy in % Ex. I-B-b-13 75070 Ex. I-A-b-3 750 80

Example I

Critical Concentration Test/Soil Insects—Treatment of Transgenic Plants

Test insect: Diabrotica balteata - larvae in soil Solvent: 7 parts byweight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of active compound in the preparation is virtuallyirrelevant, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots and these are allowed to stand at 20° C.

Immediately after preparation, 5 pre-germinated maize corns of thevariety YIELD GUARD (trademark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the test insects in question are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% efficacy).

Example J

Heliothis virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soybean shoots (Glycine max) of the variety Roundup Ready (tradename ofMonsanto Comp. USA) are treated by being dipped into the preparation ofactive compound of the desired concentration and are populated with thetobacco budworm Heliothis virescens while the leaves are still moist.

After the desired period of time, the kill of the insects is determined.

1. A compound of the formula (1)

in which W represents hydrogen, alkyl, alkenyl, alkynyl, halogen,halogenoalkyl, or alkoxy, X represents halogen, alkyl, alkoxy, alkenyl,alkynyl, halogenoalkyl, halogeno-alkoxy, or cyano; or optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkoxy, orphenylalkylthio, Y represents hydrogen, alkyl, halogen, halogenoalkyl,alkoxy, alkenyl, alkynyl, or optionally substituted aryl, Z representshydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, orcyano, A represents a direct bond; hydrogen; optionallyhalogen-substituted alkyl, alkenyl, or alkoxyalkyl; optionallysubstituted cycloalkyl or cycloalkylalkyl; or optionally halogen-,alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- ornitro-substituted aryl, or arylalkyl, B represents hydrogen or alkyl, Q¹represents hydrogen, hydroxyl, alkyl, alkoxy, alkoxyalkyl, alkylacyloxy,optionally substituted cycloalkyl, or optionally substituted phenyl, Q²represents hydrogen or alkyl, and G representshydrogen (a) or one of thegroups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ representsoptionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,alkylthioalkyl, or polyalkoxyalkyl; or optionally halogen-, alkyl-, oralkoxy-substituted cycloalkyl; or optionally substituted phenyl,phenylalkyl, or phenoxyalkyl, R² represents optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl; oroptionally substituted cycloalkyl, phenyl, or benzyl, R³, R⁴, and R⁵independently of one another each represent optionallyhalogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio,alkenylthio, or cycloalkylthio; or optionally substituted phenyl,benzyl, phenoxy, or phenylthio, and R⁶ and R⁷ independently of oneanother each represent hydrogen; optionally halogen-substituted alkyl,cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl; optionally substitutedphenyl; or optionally benzyl.
 2. A compound of the formula (1) accordingto claim 1 in which W represents hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl,ethynyl, fluorine, chlorine, bromine, C₁-C₄-halogenoalkyl, orC₁-C₆-alkoxy, X represents fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₂-C₄-alkenyl, ethynyl,C₁-C₄-halogenoalkoxy, or cyano; or optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro-, orcyano-substituted phenyl or benzyloxy, Y represents hydrogen,C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, fluorine, chlorine, bromine,C₁-C₆-alkoxy, C₂-C₄-alkenyl, or ethynyl; or represents

in which V1 represents hydrogen, halogen, C₁-C₁₂-alkyl, 1-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, orcyano; or phenyl, phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl, or phenyl-C₁-C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, orcyano, V2 represents hydrogen, fluorine, chlorine, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, or C₁-C₄-halogenoalkoxy, and V3represents hydrogen, fluorine, chlorine, methyl, or methoxy, Zrepresents hydrogen, fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkoxy, or cyano, withthe provisos that (i) W, X, and Z do not represent bromine,C₂-C₄-alkenyl, and ethynyl if Y represents V1, V2-, and V3-substitutedphenyl and (ii) no more than two of the radicals W, X, and Y representC₂-C₄-alkenyl or ethynyl, and (iii) none of the other radicals W, X, Y,and Z may represent bromine, A represents a direct bond; hydrogen;optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, orC₁-C₆-alkoxy-C₁-C₄-alkyl; optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₄-alkyl; or optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano-,ornitro-substituted phenyl, or benzyl, B represents hydrogen orC₁-C₆-alkyl, Q¹ represents hydrogen, hydroxyl, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₂-alkyl, or C₁-C₆-alkylacyloxy;optionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-, orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl; or optionally halogen,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, cyano-, or nitro-substituted phenyl, Q²represents hydrogen or C₁-C₄-alkyl, and G represents hydrogen (a) or oneof the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ representsoptionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl, orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl; optionally halogen-, C₁-C₆-alkyl-, orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl; optionally halogen-, cyano-,nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl-,C₁-C₆-halogenoalkoxy-, C₁-C₆-alkylthio-, orC₁-C₆-alkylsulphonyl-substituted phenyl; optionally halogen-, nitro-,cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, orC₁-C6-halogenoalkoxy-substituted phenyl-C₁-C₆-alkyl; optionally halogen-or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl; R² represents optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, or poly-C₁-C₈-alkoxy-C₂-C₈-alkyl; optionallyhalogen-, C₁-C₆-alkyl-, or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl; oroptionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl-, or C₁-C₆-halogenoalkoxy-substituted phenyl orbenzyl, R³ represents optionally halogen-substituted C₁-C₈-alkyl; oroptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano-, or nitro-substituted phenyl or benzyl, R⁴and R⁵ independently of one another each represent optionallyhalogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino,di(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio, C₂-C₈-alkenylthio, orC₃-C₈-cycloalkylthio; or optionally halogen-, nitro-, cyano-,C₁-C₄-alkoxy-, C₁-C₄-halogeno-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- orC₁-C₄-halogenoalkyl-substituted phenyl, benzyl, phenoxy, or phenylthio,and R⁶ and R⁷ independently of one another each represent hydrogen;optionally halogen-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl,C₁-C₈-alkoxy, C₃-C₈-alkenyl, or C₁-C₈-alkoxy-C₁-C₈-alkyl; optionallyhalogen-, C₁-C8-halogenoalkyl-, C₁-C₈-alkyl-, orC₁-C₈-alkoxy-substituted phenyl; or optionally halogen-, C₁-C₈-alkyl-,C₁-C₈-halogenoalkyl-, or C₁-C₈-alkoxy-substituted benzyl.
 3. A compoundof the formula (1) according to claim 1 in which W represents hydrogen,C₁-C₄-alkyl, chlorine, or bromine, X represents chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₂-C₃-alkenyl, ethynyl, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, or cyano, Y represents hydrogen, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₄-alkoxy,C₂-C₃-alkenyl, or ethynyl; or represents the radical

in which V1 represents hydrogen, fluorine, chlorine, bromine,C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C4-alkylthio, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro, cyano, or phenyl and V2 representshydrogen, fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-alkoxy, orC₁-C₂-halogenoalkyl, Z represents hydrogen, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C2-halogenoalkyl, or C₁-C₂-halogenoalkoxy,with the provisos that (i) W, X, and Z do not represent bromine,C₂-C₃alkenyl, and ethynyl if Y represents V1- and V2-substituted phenyl,(ii) only one of the radicals X and Y represents C₂-C₃-alkenyl andethynyl, and (iii) none of the other radicals W, X, Y, and Z mayrepresent bromine, A represents a direct bond; hydrogen; optionallyfluorine-substituted C₁-C₈-alkyl, or C₁-C₄-alkoxy-C₁-C₂-alkyl;optionally fluorine-, chlorine-, methyl-, ethyl-, or methoxy-substitutedC₅-C₆-cycloalkyl or C₅-C₆-cycloalkyl-C₁-C₂-alkyl; or optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₂-halogenoalkyl-,C₁-C₄-alkoxy-, or C₁-C₂-halogenoalkoxy-substitutedphenyl or benzyl, B represents hydrogen or C₁-C₄-alkyl, Q¹ representshydrogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C1-C₂-alkyl,or C₁-alkylacyloxy; or optionally methyl- or methoxy-substitutedC₃-C₆-cycloalkyl, Q² represents hydrogen, methyl, or ethyl, and Grepresents hydrogen (a) or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ representsoptionally fluorine- or chlorine-substituted C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, orC₁-C₄-alkylthio-C1-C₂-alkyl; or optionally fluorine-, chlorine-,C₁-C₂-alkyl-, or C₁-C₂-alkoxy-substituted 3-C₇-cycloalkyl; or phenylthat is optionally mono- or disubstituted by fluorine, chlorine,bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl, ortrifluoromethoxy; R² represents C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, orC₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionally mono- totrisubstituted by fluorine; C₃-C₇-cycloalkyl that is optionallymonosubstituted by methyl, ethyl, or Methoxy; or phenyl or benzyl, eachof which is optionally mono- or disubstituted by fluorine, chlorinebromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₃-alkoxy, trifluoromethyl, ortrifluoromethoxy, R³ represents C₁-C₆-alkyl that is optionally mono- topentasubstituted by fluorine; or phenyl that is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, trifluoro-methoxy, cyano, or nitro, R⁴ representsC₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkylamino, orC₁-C₆-alkylthio; or phenyl, benzyl, phenoxy, or phenylthio, each ofwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, nitro, cyano, C₁-C₃-alkoxy, trifluoro-methoxy, C₁-C₃-alkyl, ortrifluoromethyl, R⁵ represents C₁-C₄-alkyl, C₁-C₄-alkoxy, orC₁-C₄-alkylthio, R⁶ represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy, C₃-C₆-alkenyl, or C₁-C₆-alkoxy-C₁-C₆-alkyl; phenyl that isoptionally mono- or disubstituted by fluorine, chlorine, bromine,trifluoromethyl, C₁-C₄-alkyl, or C₁-C₄-alkoxy, or benzyl that isoptionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, ethyl, trifluoromethyl, or methoxy, and R⁷ represents hydrogen,C₁-C₆-alkyl, or C₃-C₆-alkenyl.
 4. A compound of the formula (1)according to claim 1 in which W represents hydrogen, chlorine, bromine,methyl, or ethyl, X represents chlorine, bromine, methyl, ethyl,n-propyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy,trifluoromethoxy, or cyano, Y represents hydrogen, methyl, ethyl,propyl, iso-propyl, fluorine, chlorine, bromine, or methoxy; orrepresents the radical

in which V1 represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, iso-propyl, tert-butyl, methoxy, trifluoromethyl ortrifluoromethoxy, cyano, or phenyl, and V2 represents hydrogen,fluorine, chlorine, methyl, methoxy, or trifluoromethyl, Z representshydrogen, fluorine, chlorine, bromine, methyl, methoxy, ortrifluoromethyl, with the proviso that W, X, and Z do not representbromine if Y represents V1- and V2-substituted phenyl, A represents adirect bond, hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, oriso-butyl, B represents hydrogen, methyl, or ethyl, Q¹ representshydrogen, hydroxyl, methyl, ethyl, n-propyl, iso-propyl, methoxy,ethoxy, propoxy, acetyloxy, or propionyloxy, Q² represents hydrogen,methyl, or ethyl, and G represents hydrogen (a) or one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ representsoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl, C₂-C₈-alkenyl,C₁-C₂-alkoxy-C₁-alkyl, C₁-alkylthio-C₁-alkyl, cyclopropyl, cyclopentyl,or cyclohexyl; or phenyl that is optionally monosubstituted by fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, iso-propyl, tert-butyl,methoxy, trifluoromethyl, or trifluoro-methoxy; R² representsC₁-C₈-alkyl, C₂-C₈-alkenyl, C₁-C₄-alkoxy-C₂-alkyl, or cyclohexyl; orphenyl or benzyl, each of which is optionally mono-substituted byfluorine, bromine, chlorine, cyano, nitro, methyl, tert-butyl, methoxy,trifluoromethyl, or trifluoromethoxy, R³ represents methyl, ethyl,n-propyl, or phenyl that is optionally mono-substituted by fluorine,chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano, or nitro, R⁴ represents C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino, orC₁-C₄-alkylthio; or phenyl, phenoxy, or phenylthio, each of which isoptionally monosubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁-C₂-alkoxy, trifluoromethoxy, or C₁-C₃-alkyl, R⁵ represents methyl,ethyl, methoxy, ethoxy, methylthio, or ethylthio, R⁶ representsC₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl, orC₁-C₄-alkoxy-C₁-C₄-alkyl, and R⁷ represents hydrogen, C₁-C₄-alkyl, orC₃-C₄-alkenyl.
 5. A compound of the formula (1) according to claim 1 inwhich W represents hydrogen, methyl, ethyl, chlorine, or bromine, Xrepresents methyl, ethyl, n-propyl, trifluoromethyl, or chlorine, Yrepresents methyl, trifluoromethyl, chlorine, or bromine; or phenyl thatis optionally mono- or disubstituted by chlorine and/or methyl, Zrepresents hydrogen or methyl, with the proviso that W does notrepresent bromine if Y represents substituted phenyl, A representsmethyl, ethyl, or a direct bond, B represents methyl or ethyl, Q¹represents hydrogen, methyl, methoxy, ethoxy, propoxy, hydroxyl, oracetyloxy, Q² represents hydrogen or methyl, and G representshydrogen(a) or one of the groups

where R¹ represents C₁-C₄-alkyl or represents phenyl, each of which isoptionally monosubstituted by chlorine, and R² represents C₁-C₄-alkyl.6. A pesticide comprising one or more compounds of the formula (I)according to claim 1 and one or more extenders.
 7. A method forcontrolling pests comprising allowing a pesticidally effective amount ofa compound of the formula (I) according to claim 1 to act on the pestsand/or their habitat.
 8. A process for preparing a pesticide orherbicide comprising mixing a compound of the formula (I) according toclaim 1 with one or more extenders.